Synthesis, characterization, and antifungal evaluation of diethoxyphosphoryl polyaminoethyl chitosan derivatives

Carbohydr Polym. 2018 Jun 15:190:1-11. doi: 10.1016/j.carbpol.2018.02.056. Epub 2018 Feb 22.

Abstract

Botrytis cinerea, Phytophthora capsici Leonian, and Fusarium solani are important plant pathogenic fungi which can cause great crop losses worldwide, but their control methods are limited. It is necessary to develop efficient and green fungicides from abundant marine resources. Chitosan is a non-toxic, biodegradable, biocompatible marine polysaccharide which has prospective applications in agriculture. In this paper, to increase the antifungal activity of chitosan for application, novel water-soluble functional chitosan derivatives were synthesized by grafting polyaminoethyl and diethoxyphosphoryl groups in accordance with a strategy of improving protonation potential. The derivatives were characterized by FTIR, NMR, XRD, SEM, Gaussian 09 and elemental analysis. The antifungal activities against the three fungi and the cytotoxicity were estimated in vitro. The results showed that the derivatives had better antifungal activities and water solubility than chitosan, and had good biocompatibility. They confirmed that these chitosan derivatives can be developed as antifungal agents for plant protection purposes.

Keywords: Antifungal; Chitosan; Phosphoryl; Polyaminoethyl.

MeSH terms

  • Animals
  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Antifungal Agents / toxicity
  • Cell Survival / drug effects
  • Chemistry Techniques, Synthetic
  • Chitosan / chemical synthesis*
  • Chitosan / chemistry
  • Chitosan / pharmacology*
  • Chitosan / toxicity
  • Fungi / drug effects*
  • Hep G2 Cells
  • Humans
  • Mice
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Plants / microbiology
  • RAW 264.7 Cells
  • Solubility
  • Structure-Activity Relationship

Substances

  • Antifungal Agents
  • Chitosan